Hydrochloric Acid → 2-(Imidazo[1,2-a]pyridin-7-yl)acetic acid

HRID 82194Notes

Reaction equation

C([O:3][C:4](=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][N:9]2[CH:12]=[CH:13][N:14]=[C:8]2[CH:7]=1)C.[OH-].[Na+].Cl>O1CCOCC1>[N:14]1[CH:13]=[CH:12][N:9]2[CH:10]=[CH:11][C:6]([CH2:5][C:4]([OH:15])=[O:3])=[CH:7][C:8]=12

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of imidazo[1,2-a]pyridin-7-yl-acetic acid ethyl ester (180 mg, 0.65 mmol) (Preparation 130) in dioxane (4 mL) at 0° C. was added 2 N aqueous sodium hydroxide solution (4 mL). Then reaction mixture was heated at 90° C. for 6 hours. After cooling to 0° C., the mixture was acidified to pH 4 with 2 N aqueous hydrochoric acid and extracted with 20% isopropanol in dichoromethane (8×10 mL). The combined organics were dried over sodium sulfate and concentrated under reduced pressure to afford the title compound as an off-white solid in 70% yield, 80 mg.

Workup

customThen reaction mixture
temperatureAfter cooling to 0° C.
extractionextracted with 20% isopropanol in dichoromethane (8×10 mL)
dry with materialThe combined organics were dried over sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-4b6e53b091be4fcfa060b7695112fd25
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846698B2

Reaction notes

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